Significant attention has been placed recently on the difficulties former contact sport athletes face upon their career transition out of sport as a result of head trauma (Stern, et al., 2011). Yet, many athletes, even in the midst of a difficult career transition, will look back at their career in sport fondly, expressing a sense of nostalgia for what was gained in the process of competition. Somewhat overlooked in the research examining the difficulties faced in athletic career transition is the reality that many athletes simply found their career in sport much more gratifying than life after it. As a result, athletes may find it difficult to recreate a consistent sense of enjoyment and fulfillment in their lives following sport. Even if the athlete has planned thoroughly for a career after sport, it is still possible that his or her competitive experience was simply more satisfying and rewarding than their new career. It is possible that an emotional and motivational vacuum is left behind while navigating the transition out of a satisfying career in sports. The purpose of this paper is to examine the singular sense of satisfaction, the unique emotional expressions, and the peak experiences that former contact sport athletes reported from their careers. Coupled with the examination of these experiences, I will likewise analyze the potential effect that losing the consistency of these experiences so abruptly has had on the career transitions of these athletes.